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Usage

Uses

Used in Agriculture:
Vinclozolin is used as a dicarboximide fungicide for controlling fungal infections in various crops. It helps to protect plants from diseases and ensures a healthy and bountiful harvest.
Used in Medical Applications:
Due to its antiandrogen properties, Vinclozolin has potential applications in the medical field. It can be used as a therapeutic agent for treating conditions that involve an imbalance of male hormones, such as prostate cancer or benign prostatic hyperplasia. Additionally, its hormone-disrupting properties may also be explored for other medical purposes, such as contraception or hormone-related disorders.

?Properties

Molecular formula C12H9Cl2NO3, Mr. 286.Soluble in acetone, benzene, chloroform, and ethyl acetate.

Biological functions

Vinclozolin inhibits androgen-induced gene expression in vivo.Vinclozolin treatment reduces androgen-dependent organ weights in adult rats and the anogenital distance of male pups at birth, by in utero exposure.Embryonic exposure to vinclozolin also modifies the developing testis and prostate transcriptome, including DNA methyltransferases.The metabolites of vinclozolin (M1 and M2) block AR binding to the androgen response element (ARE) and inhibit dihydrotestosterone (DHT)-induced transcriptional activation.

InChI:InChI=1/C11H11Cl2NO2/c1-3-11(2,16)10(15)14-9-5-7(12)4-8(13)6-9/h3-6,16H,1H2,2H3,(H,14,15)

Upstream product

• 152723-53-0 3-(3,5-dichlorophenyl)-5-methyl-5-vinyloxazolidine-2,4-dione 

Downstream Products

• 119759-60-3 3',5'-dichloro-2,3,4-trihydroxy-2-methylbutyranilide 

Relevant academic research and scientific papers

Kinetics and Mechanisms of Hydrolysis of Dicarboximide Fungicides in Micellar Media

The kinetics of alkaline hydrolysis of the dicarboximide fungicides procymidone, iprodione, vinclozolin, and chlozolinate (1-4, respectively) were investigated in micellar solutions containing various amounts of either sodium dodecyl sulfate (SDS), cetyltrimethylammonium bromide (CTAB), or three nonionic surfactants (two C13 alcohols and a copra amine combined with ethoxyl chains) and compared with the kinetics in aqueous media.For all compounds, the rate constants observed are slightly reduced by the SDS micellar media, showing that reactions essentially take place in the aqueous pseudophase.The CTAB micellar media speed up the hydrolysis rates with small quantities of Br- ions in the medium.As the number of Br- ions increases, the rate of reactions falls.This is characteristic of an ion exchange (OH- and Br-) at the surface of the CTAB micelles.Finally, the presence of nonionic micelles has little influence on the hydrolysis of the fungicides: the reduction in the rate of dicarboximide ring opening is attributed to micelle-substrate association.These results can be explained by means of the pseudophase kinetic model coupled with the mechanisms of hydrolysis of these fungicides in water solution.Keywords: Dicarboximide fungicide; surfactant; mechanisms of hydrolysis

Mechanisms of Dicarboximide Ring Opening in Aqueous Media: Procymidone, Vinclozolin and Chlozolinate

The hydrolysis kinetics of the dicarboximide fungicides procymidone, vinclozin and chlozolinate in neutral and alkaline solutions of pH 6.0 to 13.7 at 25 deg C have been determined conjointly by ultraviolet spectrophotometry and by high performance liquid

In vitro phase I metabolism of vinclozolin by human liver microsomes

1.?Vinclozolin (Vin) is a fungicide used in agricultural settings and is classified as an endocrine disruptor. Vin is non-enzymatically hydrolyzed to 2-[[(3,5-dichlorophenyl)-carbamoyl]oxy]-2-methyl-3-butenoic acid (M1) and 3',5'-dichloro-2-hydroxy-2-methylbut-3-enanilide (M2) metabolites. There is no information about Vin biotransformation in humans, therefore, the aim of this study was to characterize its in vitro metabolism using human liver microsomes. 2.?Vin was metabolized to the [3-(3,5-dichlorophenyl)-5-methyl-5-(1,2-dihydroxyethyl)-1,3-oxazolidine-2,4-dione] (M4) and N-(2,3,4-trihydroxy-2-methyl-1-oxo)-3,5-dichlorophenyl-1-carbamic acid (M7) metabolites, which are unstable and gradually converted to 3′,5′-dichloro-2,3,4-trihydroxy-2-methylbutyranilide (DTMBA, formerly denoted as M5). M4 and DTMBA metabolites co-eluted in the same HPLC peak; this co-elute peak exhibited a Michaelis-Menten kinetic, whereas M7 showed a substrate inhibition kinetics. The KM app for co-eluted M4/DTMBA and M7 was 24.2 ± 5.6 and 116.0 ± 52.6 μM, the VMax app was 0.280 ± 0.015 and 0.180 ± 0.060?nmoles/min/mg protein, and the CLint app was 11.5 and 1.5 mL/min/g protein, respectively. The Ki for M7 was 133.2 ± 63.9 μM. Cytochrome P450 (CYP) chemical inhibitors furafylline (CYP1A2), ketoconazole (CYP3A4), pilocarpine (CYP2A6) and sulfaphenazole (CYP2C9) inhibited M4/DTMBA and M7 formation, suggesting that Vin is metabolized in humans by CYP. 3.?DTMBA is a stable metabolite and specific of Vin, therefore, it could be used as a biomarker of Vin exposure in humans to perform epidemiological studies.

Alkaline hydrolysis of vinclozolin: Effect of humic acids aggregates in water

The influence of natural organic substances as humate colloidal aggregates in water solutions upon the chemical stability of vinclozolin has been investigated in basic media. A large inhibition (9 times-fold) has been observed and it has been rationalized in terms of a micellar pseudophase model. The observed behaviour could increase significantly the half-life of this fungicide. Moreover, these experimental results have been compared with the corresponding ones of other substances in these natural colloidal aggregates.

Chemical and Biological Transformation of the Fungicide Vinclozolin

Two mixed bacterial cultures were isolated from a French soil adapted to the dicarboximide fungicide vinclozolin. The vinclozolin was transformed by the mixed bacterial cultures according to two degradation pathways: (a) the formation of 2-[[(3,5-dichlorophenyl)carbamoyl]oxy]-2-methyl-3-butenoic acid and then 3,5-dichloroaniline or (b) the formation of 3′,5′-dichloro-2-hydroxy-2-methylbut-3-enanilide and then 3,5-dichloroaniline. The structure of 2-[[(3,5-dichlorophenyl)-carbamoyl]oxy]-2-methyl-3-butenoic acid was unambiguously established by 1H and 13C 2-D NMR analysis. A bacterial strain isolated from soil that degrades this compound was identified as a strain of Corynebacterium sp. Attempts to obtain pure vinclozolin-degrading strains via 3′,5′-dichloro-2-hydroxy-2-methylbut-3-enanilide were unsuccessful.